5-[[4-[2-[5-(2-Methyl-1,3-dioxolan-2-yl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione

Base Information

• Chemical Name: 5-[[4-[2-[5-(2-Methyl-1,3-dioxolan-2-yl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
• CAS No.: 184766-66-3
• Molecular Formula: C21H22 N2 O5 S
• Molecular Weight: 414.47
• DSSTox Substance ID: DTXSID40401597
• Mol file: 184766-66-3.mol

Synonyms:184766-66-3;5-[4-[2-[5-(2-METHYL-1,3-DIOXOLAN-2-YL)-2-PYRIDYL]ETHOXY]BENZYL]-2,4-THIAZOLIDINEDIONE;5-[[4-[2-[5-(2-methyl-1,3-dioxolan-2-yl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione;5-[4-[2-[5-(2-Methyl-1,3-dioxolan-2-yl)-2-pyridyl]ethoxy]-benzyl]-2,4-thiazolidinedione;5-[(4-{2-[5-(2-Methyl-1,3-dioxolan-2-yl)pyridin-2-yl]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione;DTXSID40401597;AKOS030255801;FT-0671710;5-(4-(2-(5-(2-Methyl-1,3-dioxolan-2-yl)pyridin-2-yl)ethoxy)benzyl)thiazolidine-2,4-dione

Chemical Property of 5-[[4-[2-[5-(2-Methyl-1,3-dioxolan-2-yl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione

Chemical Property:

• Vapor Pressure: 7.99E-16mmHg at 25°C
• Melting Point: 59-61°C
• Refractive Index: 1.607
• Boiling Point: 630.9°C at 760 mmHg
• Flash Point: 335.3°C
• PSA: 112.05000
• Density: 1.32g/cm³
• LogP: 3.14550
• Solubility.: Acetone, Chloroform, Dichloromethane, Ethanol, Ethyl Acetate
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 414.12494298
• Heavy Atom Count: 29
• Complexity: 590

Purity/Quality:

97% ^*data from raw suppliers

5-[4-[2-[5-(2-Methyl-1,3-dioxolan-2-yl)-2-pyridyl]ethoxy]benzyl]-2,4-thiazolidinedione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OCCO1)C2=CN=C(C=C2)CCOC3=CC=C(C=C3)CC4C(=O)NC(=O)S4
• Uses: An intermediate for the synthesis of the metabolite of Pioglitazone (P471000).

Technology Process of 5-[[4-[2-[5-(2-Methyl-1,3-dioxolan-2-yl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione

There total 7 articles about 5-[[4-[2-[5-(2-Methyl-1,3-dioxolan-2-yl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

5-[1-(4-{2-[5-(2-Methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-ethoxy}-phenyl)-meth-(Z)-ylidene]-thiazolidine-2,4-dione (184766-62-9) → 5-(4-{2-[5-(2-Methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-ethoxy}-benzyl)-thiazolidine-2,4-dione (184766-66-3)

Guidance literature:

With sodium hydroxide; sodium tetrahydroborate; Dimethylglyoxime; cobalt(II) chloride; In tetrahydrofuran; N,N-dimethyl-formamide; for 18h; Ambient temperature;

DOI:10.1021/jm9605694

Reference yield:

1-(6-methyl-pyridin-3-yl)-ethanone (36357-38-7) → 5-(4-{2-[5-(2-Methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-ethoxy}-benzyl)-thiazolidine-2,4-dione (184766-66-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / pTsOH / toluene / 8 h / Heating

2: 24 percent / H₂O / 5 h / 150 °C

3: 55 percent / diethyl azodicarboxylate, Ph₃P / tetrahydrofuran / 18 h / Ambient temperature

4: 56 percent / piperidine / ethanol / 18 h / Heating

5: 96 percent / NaBH₄, 1.0N aq. NaOH, CoCl₂*6H₂O, dimethylglyoxime / dimethylformamide; tetrahydrofuran / 18 h / Ambient temperature

With piperidine; sodium hydroxide; sodium tetrahydroborate; Dimethylglyoxime; toluene-4-sulfonic acid; triphenylphosphine; cobalt(II) chloride; diethylazodicarboxylate; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm9605694

Reference yield:

Methyl 6-methylnicotinate (5470-70-2) → 5-(4-{2-[5-(2-Methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-ethoxy}-benzyl)-thiazolidine-2,4-dione (184766-66-3)

Guidance literature:

Multi-step reaction with 7 steps

1: NaH / dimethylformamide; toluene / 2.5 h / 80 °C

2: 10percent aq. H₂SO₄ / 2 h / Heating

3: 92 percent / pTsOH / toluene / 8 h / Heating

4: 24 percent / H₂O / 5 h / 150 °C

5: 55 percent / diethyl azodicarboxylate, Ph₃P / tetrahydrofuran / 18 h / Ambient temperature

6: 56 percent / piperidine / ethanol / 18 h / Heating

7: 96 percent / NaBH₄, 1.0N aq. NaOH, CoCl₂*6H₂O, dimethylglyoxime / dimethylformamide; tetrahydrofuran / 18 h / Ambient temperature

With piperidine; sodium hydroxide; sodium tetrahydroborate; Dimethylglyoxime; sulfuric acid; sodium hydride; toluene-4-sulfonic acid; triphenylphosphine; cobalt(II) chloride; diethylazodicarboxylate; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm9605694

upstream raw materials:

5-[1-(4-{2-[5-(2-Methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-ethoxy}-phenyl)-meth-(Z)-ylidene]-thiazolidine-2,4-dione

1-(6-methyl-pyridin-3-yl)-ethanone

Methyl 6-methylnicotinate

ethyl 3-(2-methyl-5-pyridinyl)-3-oxopropanoate

Downstream raw materials:

Ketopioglitazone

Refernces